128708-85-0Relevant academic research and scientific papers
Ampiphilic Carbohydrate-Based Mesogens, VI: Synthesis of a Series of Alkyl 1-Thio-D-glucopyranosides and Their Regioselective Reductions to 1-Alkylthio-1-deoxy-D-glucitols
Dahlhoff, Wilhelm V.
, p. 1025 - 1027 (2007/10/02)
Alkyl 1-thio-α,β-D-glucopyranosides (hexyl to decyl, 1a-e) are prepared by reaction of penta-O-acetyl-β-D-glucopyranose with the respective thiols in the presence of diethylether-trifluoroborane, followed by deacetylation. 1a-e are converted into their tetra-O-diethylboryl derivatives 2a-e and reduced with ethyldiboranes(6) in the presence of the catalyst 9-methylsulfonyloxy-9-borabicyclononane (9-BBN-mesylate, MSBBN) to give the mesogenic 1-alkylthio-1-deoxy-D-glucitols 3a-e after deboronation.
SYNTHESIS AND LIQUID CRYSTALLINE PROPERTIES OF THE n-ALKYL 1-THIO-α-D-GLUCOPYRANOSIDES, A NEW HOMOLOGOUS SERIES OF CARBOHYDRATE MESOGENS
Doren, Henk A. van,Geest, Ralph van der,Kellogg, Richard M.,Wynberg, Hans
, p. 71 - 78 (2007/10/02)
The n-alkyl 1-thio-α-D-glucopyranosides (n-propyl to n-dodecyl) were prepared by treating 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose with an alkanethiol in the presence of boron trifluoride etherate followed by deacetylation.The n-propyl and n-butyl derivatives are not thermotropic, the n-pentyl derivative is monotropic, and the compounds with n-hexyl and longer alkyl chains are enantiotropic, the largest liquid crystalline range being from +/- 100-175 deg for the n-undecyl derivative.The transition point data are typical for smectic behavior, and X-ray data and texture observations are indicative of a smectic Ad phase.
